5-Bromo-2-(pyridin-4-YL)thiazole | 1159821-67-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-Bromo-2-(pyridin-4-YL)thiazole
• 英文别名: 5-bromo-2-pyridin-4-yl-1,3-thiazole
• CAS: 1159821-67-6
• 化学式: C₈H₅BrN₂S
• 分子量: 241.111
• InChiKey: CFJJLEWWUVGZBE-UHFFFAOYSA-N

物化性质

• 沸点：
  375.9±48.0 °C(Predicted)
• 密度：
  1.642±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Bromo-2-(pyridin-4-YL)thiazole 、 4-硼酸三苯胺 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 水 、 甲苯 为溶剂， 反应 36.0h， 以91%的产率得到N,N-diphenyl-4-(2-pyridin-4-yl-1,3-thiazol-5-yl)aniline
  参考文献：
  名称：

  Asymmetrical/Symmetrical D−π–A/D−π–D Thiazole-Containing Aromatic Heterocyclic Fluorescent Compounds Having the Same Triphenylamino Chromophores

  摘要：

  A family of linear asymmetrical D-pi-A and symmetrical D-pi-D types of thiazole-based aromatic heterocyclic fluorescent compounds bearing various electron-donating and electron-withdrawing tails (bromo, triphenylamino, pyridyl, thienyl and benzoic acid) have been designed and prepared successfully. Synthetic, structural, thermal, spectral and computational comparisons have been carried out for related compounds because of their adjustable electronic properties. It is interesting to mention that compound 2 can be prepared from 5-bromothiazole by one-pot Suzuki-Miyaura coupling and subsequent C-H activation reactions via a 5-TPA-substituted thiazole intermediate 1. X-ray single-crystal structures of six compounds indicate that they all crystallize in the triclinic P (1) over bar space group and the thiazole core exhibits different dihedral angles with its adjacent benzene ring of the triphenylamino group (3.6(3)-40.8(3)degrees). The photophysical and electrochemical results demonstrate that compound 7 exhibits high electrochemical activity with a green fluorescence emission. Meanwhile, compounds 1, 2, and 6 show high luminescence quantum yields, and compound 8 exhibits excellent thermal stability (T-d10 = 503 degrees C).

  DOI：

  10.1021/jo401384g
• 作为产物：
  描述：

  2,5-二溴噻唑 、 吡啶-4-硼酸 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 48.0h， 以75%的产率得到5-Bromo-2-(pyridin-4-YL)thiazole
  参考文献：
  名称：

  Asymmetrical/Symmetrical D−π–A/D−π–D Thiazole-Containing Aromatic Heterocyclic Fluorescent Compounds Having the Same Triphenylamino Chromophores

  摘要：

  A family of linear asymmetrical D-pi-A and symmetrical D-pi-D types of thiazole-based aromatic heterocyclic fluorescent compounds bearing various electron-donating and electron-withdrawing tails (bromo, triphenylamino, pyridyl, thienyl and benzoic acid) have been designed and prepared successfully. Synthetic, structural, thermal, spectral and computational comparisons have been carried out for related compounds because of their adjustable electronic properties. It is interesting to mention that compound 2 can be prepared from 5-bromothiazole by one-pot Suzuki-Miyaura coupling and subsequent C-H activation reactions via a 5-TPA-substituted thiazole intermediate 1. X-ray single-crystal structures of six compounds indicate that they all crystallize in the triclinic P (1) over bar space group and the thiazole core exhibits different dihedral angles with its adjacent benzene ring of the triphenylamino group (3.6(3)-40.8(3)degrees). The photophysical and electrochemical results demonstrate that compound 7 exhibits high electrochemical activity with a green fluorescence emission. Meanwhile, compounds 1, 2, and 6 show high luminescence quantum yields, and compound 8 exhibits excellent thermal stability (T-d10 = 503 degrees C).

  DOI：

  10.1021/jo401384g

文献信息

• Thiazole pyrazolopyrimidines CRF1 receptor antagonists
  申请人：Chen Zhaogen

  公开号：US20100222339A1

  公开（公告）日：2010-09-02

  The present invention relates to compounds of Formula (I), pharmaceutical compositions thereof, and use thereof as corticotropin releasing factor 1 (CRF1) receptor antagonists in the treatment of psychiatric and neuroendocrine disorders, neurological diseases, and metabolic syndrome.

  本发明涉及式(I)化合物、其制药组合物以及在治疗精神和神经内分泌障碍、神经系统疾病和代谢综合征中作为促肾上腺皮质激素释放因子1（CRF1）受体拮抗剂的用途。
• THIAZOLE PYRAZOLOPYRIMIDINES AS CRF1 RECEPTOR ANTAGONISTS
  申请人：ELI LILLY AND COMPANY

  公开号：EP2094709A1

  公开（公告）日：2009-09-02
• US8030304B2
  申请人：——

  公开号：US8030304B2

  公开（公告）日：2011-10-04
• US8481524B2
  申请人：——

  公开号：US8481524B2

  公开（公告）日：2013-07-09
• [EN] THIAZOLE PYRAZOLOPYRIMIDINES AS CRF1 RECEPTOR ANTAGONISTS<br/>[FR] THIAZOLE PYRAZOLOPYRIMIDINES CONVENANT COMME ANTAGONISTES DU RÉCEPTEUR DU CRF1
  申请人：LILLY CO ELI

  公开号：WO2008036579A1

  公开（公告）日：2008-03-27

  [EN] The present invention relates to compounds of Formula (I), pharmaceutical compositions thereof, and use thereof as corticotropin releasing factor 1 (CRF1) receptor antagonists in the treatment of psychiatric and neuroendocrine disorders, neurological diseases, and metabolic syndrome.
  [FR] La présente invention concerne des composés représentés par la formule (I), des compositions pharmaceutiques à base de ces composés, et leur utilisation comme antagonistes du récepteur du CRF1 (facteur 1 de libération de la corticotropine) pour le traitement de troubles psychiatriques et neuroendocriniens, de maladies neurologiques et du syndrome métabolique.